


Cupid's Mark

by DragonGirl420



Category: Supernatural
Genre: Dean Winchester Smut, F/M, Smut
Language: English
Status: Completed
Published: 2019-02-13
Updated: 2019-02-13
Packaged: 2019-10-27 11:38:36
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,624
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17766092
Author URL: https://archiveofourown.org/users/DragonGirl420/pseuds/DragonGirl420
Summary: Dean Winchester literally bumped into the girl of his dreams, but just as Cupid shot his arrow at them, the girl moved. Now, on February 14th, he’s got another chance to make these two crazy kids fall in love.





	Cupid's Mark

**Author's Note:**

> This is for @spnfanficpond @mrswhozeewhatsis Galentine’s Day Exchange! I got to write this for @purpleskiesandcherrypies <3 Hope you enjoy it!!

“Aw, come on, really?” Cupid moaned and looked at the ledger again. “Dean Winchester? I’ve tried… I really have! But—but he’s so stubborn!”

Cupid pouted and sighed to Heaven. “How am I supposed to get him to  _actually_ follow his heart?” Shaking his head, he thought long and hard. Finally, he realized that the only way to get close enough was to infiltrate Dean’s favorite establishment. Lucky for him, there were several other matches there, he needed to make, too. He took his orders that came straight from upstairs, made the arrangements and went about scoping out the local bar in Lebanon where he was going to have to nudge Dean Winchester’s true soulmate to start working at.

Finding Dan’s bar was a stroke of luck. It was Dean’s favorite place to go to after returning from a hunt or just a good place to kick back and have a beer when Sam was grating on his nerves. The best part was, it wasn’t too far from home.

Right around the middle of January, he noticed a new face on staff. She was only there a few nights a week, but she was cute and easily caught Dean’s eye. From the shadows, Cupid saw his chance, and took aim, hitting Dean Winchester squarely in the heart. The girl, however, bobbed and weaved at the last second, untouched by the arrow. Cupid watched in horror as she gave Dean a sweet smile but kept on moving.

 _Oh, fiddlesticks!_  Cupid wailed internally, wringing his proverbial hands over what to do…

* * *

 

Dean was writhing in his sleep again. The dream came, as it normally did, and he was helpless to stop it. It was almost every night now, and it was getting tiresome. Dean wasn’t sleeping, his waking thoughts were consumed, and when he did manage to close his eyes and rest his brain, it plagued him with dreams that he rather not experience any more.

For nearly three weeks straight, he had the same thoughts, day in and day out, and they were worse than the normal horror show that erupted in his head. These were not the day and night dreams of a man who had been to Hell, fought monsters and dealt with the Devil himself. These were thoughts of a man in love. For Dean Winchester, that was even scarier.

It had started innocently enough. A simple stop at his favorite bar in town had put her directly in his path. Dean had done nothing more than accidentally brush against her shoulder while she was carrying a try of drinks to a table. When they had briefly collided, she gracefully kept the tray’s balance, turned at him to wink and said, “Sorry, sugar. Didn’t see ya there.”

Dean had been momentarily left incapacitated by her simple action. Sure, she was beautiful—he’d seen more than his share of beautiful women—but this woman was an angel. A  _REAL_  angel; not one of the dickless wonders he was used to dealing with.

He stood, dumbfounded, as she walked away from him, her hips swaying with purpose as she delivered her table’s order. It took a minute or two of Sam tugging on his shirt to get his attention because she had all of it. Finally, Dean acknowledged his brother, nodding emphatically at whatever he was saying, and allowed himself to be pulled from the bar when their six-packs had been packaged up to go.

Since then, the girl had firmly taken root in his mind. He found himself going back to that bar to grab a drink, or pick up a bottle of whatever, just so he could see her. The next night, the dreams started. It wasn’t just a sex dream either, it was a full-on Dean Winchester patented fantasy special; lacey lingerie, handcuffs, whipped cream, a riding crop and multiple orgasms followed by… cuddling and declarations of love. When he woke, he was beyond thankful that he was in his own room at the bunker. Waking up with that big of a hardon in a motel room with his brother would have defined the word awkward.

When he saw her again after that, any chance of talking to her went out the window. Dean Winchester, Ladies Man and Deadly Hunter, became a bumbling fool. From then on, he would find himself hesitating outside of her bar, afraid to see her face to face, unsure if he would be able to hide this crazy, intense affection and attraction he had for her.

Three weeks since they bumped shoulders. Three weeks since he had been unable to make it happen with any other women; but not for the lack of trying. He didn’t even know the woman’s name, but any other woman he tried to spend an evening with was ruined by the image of this unknown waitress who dominated him in all sorts of ways.

[Originally posted by rizlow1](https://tmblr.co/ZM1TNq1dM-qgn)

 

**_February 14th_ **

Normally that meant Dean’s favorite holiday, Valentine’s Day. This year, he kicked off the fourteenth with a book of Celtic Mythology at the table in the library, trying to concentrate on the text in front of him.

“Happy Unattached Drifter Christmas,” Sam teased as he joined Dean at the table, dropping his books with a ‘thud’ startling his brother to look up.

“Jesus,” Dean moaned and looked up accusingly. “Give a guy a heart attack why don’t you. I’m getting old, you know. My heart can’t take that crap.”

Sam rolled his eyes and flipped open his book. “Find anything?” he motioned towards Deans text with his chin.

“Nah, just a bunch of stuff we already know. You?”

“Not yet. We’ve about exhausted our end. I’ll make a few calls, see what I can dig up. You outta here soon?”

“To where?” Dean asked, his brow furrowed in confusion.

Sam snorted a laugh. “Uh, to find some poor woman to torture for a night?”

“Bite me, alright? Women love me.”

“Mhm, that’s why you’ve been a grumpy bastard, right? Cause all those girls you’ve been seeing…. Ohhhh right. There haven’t been any.”

“I hate you.”

“Seriously, Dean. Just go to the damn bar and ask her out. Three weeks of this has been enough.”

“Three weeks, it hasn’t been thre—” Dean stopped and did some calculations in his head before speaking again. “Three weeks, four days and about five hours…”

Sam raised his expression, his jaw slacked open in disbelief. “You’re right. It hasn’t been three weeks, it’s been longer!” he shook his head, the smile only growing and deepening his dimples. “I’ve never seen you like this over a girl you haven’t even talked to.”

“I’ve talked to her!” he said, then relented and changed his answer. “Kinda.”

“Dude, you turn into Porky Pig when you get around her,” Sam teased and mocked Dean in his best Porky impression. “We-we-we-well, hi there! Ai-ai-ain’t you pr-pr-pretty!”

“I really,  _really,_ hate you,” Dean admonished, standing up from the table. “You know what? Fine. I’m going over there, and I’m going to ask her out. Happy?”

Sam nodded. “Yes. If it gets you out of this weird funk you’ve been living in, I will be eternally happy to see you get laid.”

“Why couldn’t I have been an only child?” he mumbled to himself, raising his eyes to the ceiling and slightly shaking his head. Dean turned to leave the room, and without looking back called out “Don’t wait up!”

* * *

 

The Impala rolled to a stop along the curb across the street from the local bar where she worked. He could hear the music from inside spilling out onto the street. He paused before walking in and took in a deep breath. Looking down at his clothes, he wondered if he should have changed first. Dean was never the type to worry too much about his wardrobe, but suddenly he was concerned he looked like he just got off from his shift at the mill and not like a guy on a mission to win over a girl.

“What the hell is wrong with me?” he asked himself, shaking off the self-doubt that muddled around in his head. “Let’s do this.”

The bar was filled with local faces, some he recognized from around town, others he didn’t, but all of them were there to drink and have a good time for Valentine’s Day. Dean scanned the room, hoping to find her in the crowd, but there was no sign of her; just various couples making out, flirting, or having a few drinks. Walking over to the bar, he kept his eyes peeled, but there was no trace of his crush. When he finally reached the bar through the crowd, he flagged down the bartender.

“Dan! Double shot of whiskey and whatever you got on tap,” he called out over the noise.

The bartender nodded in acknowledgment and went about getting his drinks. Dean turned to face the room, leaning back against the old mahogany wood and continued to watch the sea of faces for the one he was looking for.

The jukebox faded out one song, and before the next queued up, a burst of noise came from the back corner of the bar, where the ‘Employees Only’ door lived. A crash of broken glass and shouts ensued and when Dean’s attention went that way, he finally caught sight of her.

“Whoa! Watch it, lady!” one of the guys roared, causing the entire bar to stop and take notice.

Dean immediately cut through the gathering of people who stopped and watched the scene play out. The waitress he’d been looking for was scrambling to clean up a gigantic mess. He didn’t see it happen, but he was at her side in seconds, trying to make room and help her clean up the shards of glass.

Dean took her hands in his and saw they had a few small cuts. “Hey, leave it for a second, alright,” he said, soft enough for only her to hear. That’s when she made eye contact with him. A slow, grateful smile unfurled on her face as she saw him there.

“Come on, sweetheart, let’s get your hands looked at, make sure you’re alright,” Dean said, gingerly taking her palms. He didn’t even realize that the usual bout of nerves he had around her had faded completely. The moment she had made eye contact with him while hovering over broken glass, all of that was gone and he was completely at ease.

Making physical contact with her, after all this time dreaming about it, made everything else fall away. The noise and swell of the music now behind him, Dean couldn’t hear anything as the entirety of his focus was on her.

“What’s your name?” he asked, turning her palms over to check the backs of her hands.

“(Y/N),” she mumbled, “thank you for your concern, sugar, but I’m okay. I just need to clean this up.”

“I’ll take care of it, you go back to the office, or wherever and get yourself a couple band aids.”

“It’s fine, I—”

“Please, I insist,” Dean said, giving her his softest gaze and smile.

The bartender sidled up along side them and began sweeping the glass. “Go, (Y/N), he’s right, a couple of those are gonna be bleeders.”

“Come on, I’ll go with you. I’m great at first aid,” he said proudly, immediately regretting it.

“Alright,” she relented and walked back through the ‘Employees Only’ door as Dean followed.

* * *

 

From the recesses of the corner, Cupid smiled. He sighed with relief that this time, he had hit his secondary target, perfectly.

 _I just feel bad I made her drop tray_ , he thought as he scratched Dean Winchester’s and (Y/F/N Y/L/N)’s from his ledger. He clutched to his chest, grinning warmly, just as they disappeared into the back room together.

Once it closed, he closed his eyes dreamily and patted himself on the back for a job well done before disappearing to return to Heaven.

 

* * *

“Thanks for the assist out there,” you said, as he pulled back the wrapping and laid the band aid across the worst of the cuts.

“It’s my pleasure. There, all done,” he smiled after applying the last one. His hand lingered on yours.  _I hope he never removes it_ , you thought, and felt your body flash warm as he held your hand.

“Thank you. I really could have managed it, but I sure do appreciate your kindness,” you said, gently placing your other hand on his knee.

He blushed a little and seemed to get slightly nervous. “I’m, uh, Dean, by the way.”

“Dean… yes. I’ve seen you around here a lot. Its nice to finally have a name for the very handsome face.”

And what a face he had. You knew who he was, you had known who he was the first night you bumped into each other. You thought by the way he had looked at you, he might try to flirt, but he never did. In fact, he would avoid you when he could, though his eyes never seemed to be able to leave you. You certainly didn’t mind it. But as the weeks went on, he never uttered more than a few stumbling words at you before grabbing his beer and running out the door.

The door to the office opened, and Dan came in, shaking his head when he saw the band aids on your hands. “Look, (Y/N), why don’t you head home. I called Trish, she’s been wanting the extra shift, and I’d rather you just call it a night.”

“I’m fine to keep working, Dan. Honest.”

“You’ll still get your usual pay and cut of tips, no worries, okay?”

“Dan—”

“Please, (Y/N), I insist. Go home for tonight, come back for your shift tomorrow.”

You sighed and relented. “Fine. I’ll go home.”

From the corner of your eye, you saw Dean’s face fall in disappointment, which made you wonder if maybe he did like you, after all.

Dan said goodnight, shook Dean’s hand and told him that the drinks he had ordered were on the house. Once he left the room and closed the door, you stood up from the desk chair and grabbed your personal belongings from the bottom drawer.

“Well, this night took a turn,” you laughed, but there wasn’t much humor in it.

Dean shifted nervously on his feet. “I’d say. Its early though. If you didn’t want to go home, I could, maybe… do you need a ride or anything? Are you hungry? Did you eat anything? We can go grab some food, or—”

“Dean,” you jumped in, “if you’re trying to ask me out, the answer is yes.” Your heart was pounding out of your chest, but you did your best to remain calm. You’d been hoping for this for a while and now that it was happening, you found yourself also a pile of nerves.

“Really? That’s great,” he replied and smiled sheepishly. “That’s really, really awesome. I know its last minute and all—”

“That’s okay,” you said, jumping in. “Honestly, the second I looked up and saw you sitting there, I just… I don’t know… immediately wanted to come over and say hi.”

“But then pool table guy bumped you, and—”

“No, he didn’t actually. That was all me being a klutz. I saw you standing at the bar and I froze. Then, it was weird, actually, I felt like I got hit by something and it just startled me. So much so that I dropped the tray.”

You laughed, and thought Dean would find you completely insane, but he simply nodded. “I think I know what you mean.”

“So, where should we go?” you asked, anxious to get out of there and be somewhere quiet with him. “Everywhere decent is going to be packed to capacity.”

Dean thought for a second. “How do you feel about maybe, possibly, being a little cold. But I promise it will be worth it.”

“I have a coat, I can tolerate cold,” you grinned. When Dean put out his hand, you took it and he entwined his fingers with yours, taking special care not to aggravate your cuts.

[Originally posted by soluscheese](https://tmblr.co/ZzILit2SEzeZa)

 

Thirty minutes and a stop at the Gas ‘n Sip later, Dean was directing his car into a wide-open field a few miles out of town. The February air was cold, but it wasn’t as bad as it could have been. From the trunk, Dean brought out two large blankets and laid one on the ground right near the front of the car. He motioned for you to sit before going to the back seat to retrieve the bag from the gas station.

“Alright,” he said, sitting down on the blanket. “Have a seat.”

You did and within a moment of sitting beside him, he took the second blanket and wrapped it around your shoulders, then his own. From inside his jacket pocket, he produced a flask and handed it to you.

“You just happened to have two big, fluffy blankets in your trunk. Sure you weren’t planning this?”

“I have, but not this, exactly,” he flashed you a sexy smile and wiggled his eye brows playfully. “My brother and I travel a lot for work. So, I keep them there in case we gotta crash in the car.” Dean rifled through the plastic bag and removed two Hostess pies, two bags of chips and other assorted snacks. “Sorry its not a proper dinner, but that’s what I get for asking you out last minute.”

You shrugged. “Hey man, I was pulling a double shift and closing down the bar on Valentine’s day. I’ll take this, happily. Especially if I get to hang out with you.”

Dean shook his head in disbelief. “I did come to the bar to ask you out, but I certainly didn’t think we’d do it tonight. Can’t say I’m upset with how things turned out though.”

“Me either,” you breathed and raised his flask before taking a swig and handing it back. The liquor burned on your throat, but it felt nice and warm going down. “So, not to make this awkward or anything, but why did it take you so long to ask me out?”

“You made me nervous,” he admitted bashfully. “There was just something about you I couldn’t get out of my head. Then when I’d see you…” he shrugged.

“Can I be honest with you?”

“Of course.”

“You’ve been on my mind a lot, lately. And that’s not usual for me by the way, especially with some guy I don’t know.” You paused and looked up at the sky that was dotted with thousands of stars and a waning moon. You could feel his eyes on you, and as much as you wanted to gaze into them, you were afraid to look and just kept babbling. “I get hit on by some creeper every night, and every night, I wished it was you coming in to see me.”

Dean closed his eyes and snorted a laugh. “If you had any idea how many times I came in, specifically to see you…”

“So, what you’re saying is, we’ve both liked each other for a while, but each have been too scared to make a move?”

“Seems that way,” he said, pulled from the flask and handed it back to you.

“Now, its Valentine’s Day, of all days, and here we are. Sitting under the stars with a picnic and a flask.”

“What can I say, my timing is amazing,” he teased. Dean let his eyes wander over your face, and when he put an arm around your shoulders, you immediately leaned into him.

You sighed contently against the stranger you’d been crushing on for weeks. “I’m suddenly not nervous anymore.” You felt Dean’s body shift against yours, it stiffened then relaxed again, his grip on your shoulder tighter.

“I’m not either,” he rasped. You felt him shift again. Dean loosened his arm around your shoulders, and gingerly guided your face up towards his with his other hand. “For the first time in weeks, I don’t feel like an idiot around you. And, I’d really like to kiss you now…”

He left you speechless. The whole night left you completely, utterly, speechless. For almost a month, you had seen his face in the bar on countless occasions. A few quick conversations here and there, made you interested in him, but the way he was making you feel in that moment, didn’t seem possible to happen in such a short amount of time.

Dean took your silence into another moment of consideration. You wanted to kiss him,  _needed_ to, so you did. You tilted your head, rested your hand against his knee, then sat up more and pressed your lips to his.

 _God he’s soft_ , you thought as you kissed him,  _So deliciously, soft_.

Taking it slow, enjoying the parting and coming back together of your lips. His hands were tentative but started to explore other parts of your body as the comingling of your mouths continued. Your heart began to beat faster the further his hand traveled up your leg stretched out before you. When Dean pulled back from you and sat up on his knees, you didn’t hesitate to reposition yourself, for him to lay you down.

Dean did just that, then took the blanket and tossed it around his shoulders like a cape, before leaning down and hovering over you. You thought you could hear his heart pounding, just as loudly as yours. His eyes frantically scanned over your features before he caressed the side of your face.

“I feel like I’ve been waiting for you forever,” he mumbled. Before you could respond, he dove back to your lips and kissed you.

He kissed you like no one ever had before. It was soft and moist, and the longer it continued, the heavier you both were breathing. The February air didn’t phase you one bit, because the moment his tongue broke through, pairing with yours, a depth of heat rose and filled the space you shared under the blanket with him. Dean moaned into your mouth, his hips twitching as your leg curled up around his thighs. Your arms were wrapped up around him, his were moving all over your body.

“Jesus,” he breathed, parting for a moment of air. “What the Hell…”

“What? Is everything okay?” you were trying to catch your own breath, but worried he was regretful.

“No, its just… where did this come from?”

“I don’t know. Chalk it up to Valentine’s Day?”

Dean chuckled. “Sweetheart, it could be the middle of July or the dead of winter, and I’d still want to carry you to the backseat of my car and tear your clothes off right now.”

You smirked and raised a challenging brow. “So, what’s stopping you?”

“Good God, where have you been all my life?” he asked, scrambling to sitting back up on his knees. “But, I mean, we just met. I don’t want to rush—”

You got up and met his eye line as you sat up on your knees. “Have you ever just felt like something was right? Meant to be? That’s how I feel right now and, you know what, who knows or cares why.”

Dean exhaled and nodded slowly. “You’re absolutely right.”

He stood and reached a hand down to help you up. When you were on your feet, Dean kissed you again. The kissing was nice, he was the best you’d ever had the pleasure of enjoying, but you wanted more. You  _needed_  more. Taking his bottom lip between yours, you released it slowly, grazing your teeth as you did, which seemed to trigger something in him.

Dean took your hand and hurriedly pulled you around to the passenger side of the car, not forgetting to take the one blanket with him. Minutes later you were straddling his lap in the backseat of his Impala, as his lips covered the swell of your breasts and his hands drew down the silk cup of your bra. Your hands were around the back of his neck, pressing his head into your chest; your head rolling back as his lips clamped down around your nipple.

You could feel his erection growing through his jeans, the harder it pressed into your thigh, the more you wanted to feel it inside you. Your ache for him was maddening, and you were starting to feel a bit lightheaded from his touch. It felt crazy, absolutely insane in fact, to desire someone you barely knew, the way you did. Yet…

“ _Dean_ ,” you moaned in a delicate whisper.

He didn’t raise his head but trailed his lips across your chest and back up to your neck. Dean gripped your neck, pulling it down so his mouth was on your ear. “Say my name again and tell me what you want, sweetheart.”

“I want to see you,” you rasped and ran your hands down his chest, stopping at his belt buckle. You pulled your head back to catch his gaze. His green eyes full of lust, his nostrils flaring slightly in excited anticipation of what was to come. He moved his hips and pushed down his jeans, allowing his cock to spring free. “I want to taste you,” you purred and stood up as best you could and worked at removing your own jeans. “Then, I want to feel you inside me…  _Dean._ ” His name fell from your lips with a breathy expulsion.

Bending over, you brought your lips to the tip of his dick as you let your clothes slip to the floor of the car. Once free of any restraints, the apex of your thighs craved the feeling of him slipping deep inside you. But first, you wanted him to want you just as badly. He tried to guide you back to his lap, but you wanted to taste him first. The urge to be with him, touch every square inch of him just drove you to act on instinct. No doubt or hesitation crept in. You wanted him, all of him, and from the way he was digging his fingers into your legs, and the way his eyes were devouring you, you thought he felt the same way.

Your mouth covered as much as of him as it could. Dean snaked his hand around to the inside of your thighs and reached up into your folds, making your grip on his shaft tighten in response.

“Fuck,” he moaned, his mouth slacked open as his head rolled back against the seat.

His fingers worked you over, slowly at first, but as your hips moved involuntarily along with his motion, he went faster. Lasting for only another moment, you felt the first flutters of your climax and abruptly pulled his hand from you.

“Not yet,” you commanded, releasing his dick with a pop of your lips.

You hovered back over his lap, meaning to tease him, but Dean would have no teasing. He took your hips and positioned himself, easily sliding up into your entrance, but not quite filling you. He was gentle, and though you were dazed with how much you wanted him, the way he was making you feel was euphoric. It wasn’t just the sensation of the sex, it was the intimacy that you felt as he held your gaze. It was the way his hands caressed the skin on your thighs, up your sides, cupping your breasts, then moving back down the way he came as you rocked against him.

Biting on his lower lip, he thrusted up into you, hitting your hilt and making you inhale sharply. Your breath released in a quiver, making him grin a satisfied smirk. It only last, a minute, as you moved your hips not just back and forth, but side to side. The friction against your clit was enough to finally break your resolve, and your walls to flutter around him.

“Jesu—” your breath faltered as your climax ruptured around him. It didn’t phase Dean’s penetrating thrusts as he bounced you on his lap, and you gripped his shoulders holding on for dear life.

Between his movements and your orgasm, you felt lightheaded and cried his name in a raspy moan. Dean pushed you into him, his head buried in your chest as he quickly lifted you off him before his own climax expelled all over his abdomen. He held you that way until he was able to get his breathing under control, but even once he did, he didn’t release you right away.

You peeled yourself from him, sitting back just enough to take his face in your hands and turn it up to yours.

“That was intense,” you said, your voice soft and dreamy. You felt like you were under a spell, under  _his_  spell. A sensation you never had before and thought you could live in forever.

“Very,” he replied, and ran his tongue slowly over his bottom lip. “Are you alright?”

“Better than,” you smiled, and gently kissed his lips.

Dean reached over and grabbed the blanket, wrapping it around you both as you climbed off his lap and snuggled into his side.

“Cold?” he asked, wrapping an arm around your shoulder and kissing the top of your head.

“No, not even a little.” You drew the blanket tighter around you, enjoying the cocoon it created for you and Dean.

There was a brief, awkward silence as you just starred at each other, unsure of what to say. Its not that there were questions rolling around in your head, or that you were wondering what came next. There was an unfamiliar level of certainty that what had just transpired meant something, more than just a one-night stand on a very triggering holiday.

“Dean?”

“Yeah?”

“I’m not exactly sure how to ask this, but—”

“You wanna know what this means?”

“No. It doesn’t matter what it means… because it meant something. At least that’s how I feel. You don’t just meet someone and have that intense of a, um…” you felt your skin flash hot with a moment of embarrassment “encounter, without it meaning something. But that wasn’t what I was going to ask.”

“Oh,” he said, and looked away for a moment, his expression thoughtful in contemplation. “What did you want to ask then?”

“The snacks. We left them outside and honestly, I’m starving. Maybe we should head back to my place. I could cook us something… maybe we could watch a movie or just have sex again?”

“Or all three?”

“Yeah, that works, too,” you laughed and leaned forward to retrieve your pants from the floor.

Once you were both properly clothed again, Dean grabbed the remains of the picnic and threw it in the back seat while you gazed up at the stars. Just above the horizon, a few meteors streaked across the sky. You felt a soft smile touch your lips, not just because of the celestial show before you, but because of who you were sharing it with.

“Some night, huh?” he asked, wrapping his arms around your shoulders from behind and guiding you to lean back into him.

“Yeah, craziest night of my life, honestly.”

“Do you mind a little crazy every now and again?”

“Depends. Good crazy, or bad crazy?”

“What if I said a little of both?”

“You’re being cryptic, but I kinda dig it. I could handle both, why do you ask?”

Dean shrugged and looked up at the stars. “I’d like to see you, more. A lot more, actually. But my life… it gets—”

“Crazy?”

He chuckled and brushed a piece of hair the February breeze brought onto your face. “That’s putting it mildly, but yeah. Think that’s something you’d be up for?”

You thought about what he said and realized that the only answer in your head was yes. Yes, you think you would be up for just about anything if he was with you. Your first date was a testament to that.

“If that,” you motioned towards the backseat “was just the beginning of this? Darlin’ I think I could handle just about anything.”

* * *

 

Dean kissed her, his heart was already experiencing a level of attachment to a woman he didn’t think would ever be meant for him. There was no rhyme or reason to it. It was as if Cupid himself put a spell over them. Even if the happy little angel did have a hand in making it happen, Dean was still pretty damn happy. So much in fact, he would forgive the interference.

Opening the car door for (Y/N), he waited until she was settled before kneeling down at the open door.

“(Y/N), I want you to know that, it did mean something to me, too. I don’t know where this goes, what really happens next. But I don’t care. Sometimes life is too damn short to question everything.” He shrugged, took her hand and kissed the back of it.

“Amen to that… Shit. I don’t even know your last name,” she laughed and seemed slightly embarrassed.

“Winchester. Yours?”

“(Y/L/N),” she smiled and squeezed his hand.

“Well alright, Ms. (Y/L/N). Shall we go?”

“Yes, I’m starving!”

He stood up, leaned in to kiss her lips again before closing the door and walking around to get in behind the wheel. Before he got in, he looked back up to the sky and smiled.

“Goodbye Unattached Drifter Christmas… hello Saint Valentine…” the corner of his mouth cocked up into a smirk and he jumped into the car, ready to whisk his new girl off to continue their date.


End file.
